1612-76-6Relevant articles and documents
Synthesis of 2-amino-5-substituted-1,3,4-oxadiazoles using 1,3-dibromo-5,5-dimethylhydantoin as oxidant
Rivera, Nelo R.,Balsells, Jaume,Hansen, Karl B.
, p. 4889 - 4891 (2006)
A scalable synthesis of 5-substituted-2-amino-1,3,4-oxadiazoles via oxidation of a thiosemicarbazide precursor is described. The thiosemicarbazide intermediates are easily accessed from the corresponding acid chlorides. Oxidative cyclization using 1,3-dibromo-5,5-dimethylhydantoin as the primary oxidant, in the presence of potassium iodide, gives a variety of oxadiazoles in good yields. This methodology utilizes a commercially inexpensive and easily handled oxidant.
Synthesis of N,N-Disubstituted 3-amino- 1,2,4-triazoles
Katritzky, Alan R.,Rogovoy, Boris V.,Vvedensky, Vladimir Y.,Kovalenko, Katherine,Steel, Peter J.,Markov, Victor I.,Forood, Behrouz
, p. 897 - 903 (2001)
A general method for the synthesis of N,N-disubstituted 3-amino-l,2,4-triazoles 5 from di(benzotriazolyl)methanimines 1 and 1′, hydrazine and substituted hydrazines is developed. The desired compounds were prepared regioselectively under mild conditions b
N,N-dialkyl-N′-chlorosulfonylchloroformamidines in heterocyclic synthesis. II. Thiazolo-, thiadiazolo-, and oxadiazolo-fused [1,2,4,6]thiatriazine dioxides
Fallon, Gary D.,Francis, Craig L.,Johansson, Katarina,Liepa, Andris J.,Woodgate, Ruth C. J.
, p. 891 - 900 (2005)
N,N-dialkyl-N′-chlorosulfonylchloroformamidines 1 were treated with 2-aminothiazoline, 2-aminothiazoles, 2-aminobenzothiazoles, 2-amino-1,3,4- thiadiazoles, and 2-amino-1,3,4-oxadiazoles to give a 6,7-dihydrothiazolo[3,2-b] [1,2,4,6]thiatriazine dioxide 3
Synthesis, antibacterial activities and molecular docking study of thiouracil derivatives containing oxadiazole moiety
Cui, Peng-Lei,Zhang, Di,Guo, Xiu-Min,Ji, Shu-Jing,Jiang, Qing-Mei
supporting information, p. 1754 - 1762 (2021/04/09)
A series of novel thiouracil derivatives 9 containing an oxadiazole moiety have been synthesized by structural modification of a lead SecA inhibitor, 2. These compounds have been evaluated for their antibacterial activities against Bacillus amyloliquefaciens, Staphylococcus aureus and Bacillus subtilis. Among them, compounds 9g and 9n exhibited promising antibacterial activities against the tested strains. Compound 9g was also tested for its inhibitory activities against SecA ATPase, and the IC50 value of compound 9g was 19.9 μg/mL, lower than that of compound 2 (20.8 μg/mL). Molecular docking work indicates that compound 9g likely occupies the pocket formed by SecA IRA2 and NBD domain.
Synthesis of 1,3,4-oxadiazoles as selective T-type calcium channel inhibitors
Zhang, Man,Zou, Bende,Gunaratna, Medha J.,Weerasekara, Sahani,Tong, Zongbo,Nguyen, Thi D.T.,Koldas, Serkan,Cao, William S.,Pascual, Conrado,Xie, Xinmin Simon,Hua, Duy H.
, p. 145 - 164 (2020/02/04)
– Neuropathic pain, epilepsy, insomnia, and tremor disorder may arrive from an increase of intracellular Ca2+ concentration through a dysfunction of T-type Ca2+ channels. Thus, T-type calcium channels could be a target in drug discovery for the treatments of neuropathic pain and epilepsy. From rational drug design approach, a group of 2,5-disubstituted 1,3,4-oxadiazole molecules was synthesized and their selective T-type channel inhibitions were evaluated. The synthetic strategy consists of a short sequence of three reactions: (i) condensation of thiosemicarbazide with acid chlorides; (ii) ring closing by 1,3-dibromo-5,5-dimethylhydantoin; and (iii) coupling with various acid chlorides. 5-Chloro-N-(5-phenyl-1,3,4-oxadiazol-2-yl)thiophene-2-carboxamide (11) was found to selectively inhibit T-type Ca2+ channel over Na+ and K+ channels in mouse dorsal root ganglion neurons and/or human embryonic kidney (HEK)-293 cells and to suppress seizure-induced death in mouse model. Consequently, compound 11 is a useful probe for investigation of physiologic and pathophysiologic roles of the T-channel, and provides a basis to develop a novel therapeutic to treat chronic neuropathic and inflammatory pains.
